4573. Guggulsterone

Nomenclature

CAS number: 95975-55-6
Pregna-4,17(20)-diene-3,16-dione.
C21H28O2; mol wt 312.45.
C 80.72%, H 9.03%, O 10.24%.

Description and references

Bioactive component in guggulu, q.v., the gum resin of the Ayurvedic medicinal plant, Commiphora mukul, Burseraceae, used in treatment of lipid disorders. Both the E- and Z- isomers are naturally occurring and bioactive. Synthesis and stereochemistry: W. R. Benn, R. M. Dodson, J. Org. Chem. 29, 1142 (1964). Isoln from guggulu: V. D. Patil et al., Tetrahedron 28, 2341 (1972). HPLC determn of isomers in serum: N. Verma et al., J. Chromatogr. B 708, 243 (1998). LC determn of isomers in commercial guggulu formulations: M. Nagarajan et al., J. AOAC Int. 84, 24 (2001). Inhibition of the bile acid receptor FXR and cholesterol lowering activity: N. L. Urizar et al., Science 296, 1703 (2002). Brief review of proposed mechanism of action: C. J. Sinal, F. J. Gonzalez, Trends Endocrinol. Metab. 13, 275-276 (2002).

Chemical structure

Derivative

E-Form.

Nomenclature

CAS number: 39025-24-6

Properties

Prisms from aq methanol, mp 170-171.5°. [α]D26 30° (c = 1 in chloroform). uv max (methanol): 241 nm (ε 27600).

Derivative

Z-Form.

Nomenclature

CAS number: 39025-23-5

Properties

Crystals from aq methanol, mp 188-190°. [α]D26 61° (c = 1 in chloroform). uv max (methanol): 241 nm (ε 25000).